Second example is broken. Not only "specification" is broken, but also size of apps does not consider size/installation problems of VMs.
Now to first example:
1) How do you protect Python apps from copyright abusers?
2) Py2exe works, but if one expects python already installed: which version of python? Which version of Java? .net?
3) It is not easy to write C extensions to Python programmer. It is easy for C/C++ programmer pick up Python, but not other way around.
This [The app is not free.] part also makes me wonder, what that means.
Where I agree is that every sufficiently large C++ program is worth to stary writing in Python.